Glycogen is a short-term energy storage material in animals. In mammals, glycogen occurs in muscle and liver tissues. It is comprised of 1,4-glucan chains, highly branched via α-1,6-glucosidic linkages with a molecular weight of 106-108 Daltons. Glycogen is present in animal tissue in the form of dense particles with diameters of 20-200 nm. Glycogen is also found to accumulate in microorganisms, e.g., in bacteria and yeasts.
Phytoglycogen is a polysaccharide that is very similar to glycogen, both in terms of its structure and physical properties. It is distinguished from glycogen based on its plant-based sources of origin. The most prominent sources of phytoglycogen are kernels of sweet corn, as well as specific varieties of rice, barley, and sorghum.
Methods of producing glycogen and phytoglycogen from different sources are known in the art.
Various methods have been developed to isolate glycogen and phytoglycogen from living organisms.
Known methods include extraction from animal tissues, particularly from marine animals, especially mollusks, because of their ability to accumulate glycogen. See for example, methods described in U.S. Pat. Nos. 5,734,045, 5,597,913; Japanese patent application JP2006304701; Malcolm, J. The Composition of some New Zealand Foodstuffs. Trans Proc R Soc N Z. 1911 44:265-269; Ward J F et al. Extractions of Glycogen from Soft Shell Clams (Mya arenaria). Chesapeake Sci. 1966, 7(4):213-214; Wary C et al. 1H NMR spectroscopy study of the dynamic properties of glycogen in solution by steady-state magnetisation measurement with off-resonance irradiation. Carbohydr Res. 1998, 306(4):479-91; Matsui M, et al. Fine structural features of oyster glycogen: Mode of multiple branching. Carbohydrate Polymers, 1996, 31(4): 227-235; Sullivan M A et al. Improving size-exclusion chromatography separation for glycogen. Journal of Chromatography A, 2014. In press; the disclosures of which are incorporated by reference in their entirety.
Glycogen can also be extracted from mammals and, in particular from liver or muscle tissue, according to various methods see e.g. Popovski S. et al. The mechanism of aggregation of β-particles into α-particles in rat liver glycogen. Biochemical Society Transactions (2000) 28, Part 5, A336; Sullivan M A et al. Nature of alpha and beta particles in glycogen using molecular size distributions. Biomacromolecules. 2010 Apr. 12; 11(4):1094-100; Wanson J C & Drochmans P. Rabbit skeletal muscle glycogen. A morphological and biochemical study of glycogen beta-particles isolated by the precipitation-centrifugation method. J Cell Biol. 1968. 38(1):130-50; Somogyi, M. The solubility and preparation of phosphorus- and nitrogen-free glycogen. J. Biol. Chem. 1934.104: 245; Geddes R et al. The molecular size and shape of liver glycogen. Biochem. J. 1977. 163: 201-209; Devos P et al. The alpha particulate liver glycogen. A morphometric approach to the kinetics of its synthesis and degradation. Biochem. J. 1983, 209:159-165; Orrell S A & Bueding E. A Comparison of products obtained by various procedures used for the extraction of glycogen. J Biol Chem. 1964, 239:4021-4026; Bröjer J T et al. Effect of extraction time and acid concentration on the separation of proglycogen and macroglycogen in horse muscle samples. Can J Vet Res. 2002, 66(3):201-6; Bell D G & F G Young. Observations on the chemistry of liver glycogen. Biochem. J. 1934, 28:882-0; Stetten M R et al. A comparison of the glycogens isolated by acid and alkaline procedures. J Biol Chem. 1958, 232(1):475-488; Wary C et al. 1H NMR spectroscopy study of the dynamic properties of glycogen in solution by steady-state magnetisation measurement with off-resonance irradiation. Carbohydr Res. 1998, 306(4):479-91; Laskov R. & E. Margoliash. Properties of high molecular weight glycogen from rat liver. 1963. Bull. Res. Counc. Isr. 11: 351-362; Haverstick D M & Gold A H. Isolation of a polydisperse high-molecular-weight glycogen from rat liver. Anal Biochem. 1981 February; 111(1):137-45; Parker G J et al. AMP-activated protein kinase does not associate with glycogen alpha-particles from rat liver. Biochem Biophys Res Commun. 2007, 362(4):811-5; Sullivan M A et al. Improving size-exclusion chromatography separation for glycogen. Journal of Chromatography A, 2014. In press; the contents of each of which are incorporated by reference in their entirety.
Phytoglycogen can also be isolated from plant material according to various methods. See, for example, U.S. Pat. No. 5,895,686 and European patent EP0860448B1, and Wong, K S et al. Structures and properties of amylopectin and phytoglycogen in the endosperm of sugary-1 mutants of rice. J. Cereal Sci. (2003) 37: 139-149; Fujita N et al. Antisense inhibition of isoamylase alters the structure of amylopectin and the physicochemical properties of starch in rice endosperm. Plant Cell Physiol 2003, 44 (6): 607-618; which describe processes of isolating phytoglycogen from kernels of rice Verhoeven, T. et al. Isolation and characterisation of novel starch mutants of oats. Journal of Cereal Science, 2004, 40 (1): 69-79, which describes the isolation of phytoglycogen from oats; Burton R A et al. Starch granule initiation and growth are altered in barley mutants that lack isoamylase activity. Plant J. 2002, 31(1):97-112, which describes the isolation of phytoglycogen from barley; International patent application publication no. WO 2013/019977; U.S. Pat. No. 6,451,362; Rolland-Sabaté A., et al. Elongation and insolubilisation of alpha-glucans by the action of Neisseria polysaccharea amylosucrase. J Cereal Sci. 2004, 40:17-30; Dinges J R, et al. Molecular structure of three mutations at the maize sugary1 locus and their allele-specific phenotypic effects. Plant Physiol. 2001, 125(3):1406-18; Morris D L & CT Morris. Glycogen in sweet corn. Science. 1939, 90(2332):238-239; Miao M, et al. Structure and digestibility of endosperm water-soluble α-glucans from different sugary maize mutants. Food Chem. 2014, 143:156-62; Miao M, et al. Structure and physicochemical properties of octenyl succinic esters of sugary maize soluble starch and waxy maize starch. Food Chem. 2014, 151:154-60; Powell P O, et al. Extraction, isolation and characterisation of phytoglycogen from su-1 maize leaves and grain. Carbohydr Polym. 2014, 101:423-31; Sullivan M A, et al. Improving size-exclusion chromatography separation for glycogen. Journal of Chromatography A, 2014. In press; Scheffler S L, et al. Phytoglycogen octenyl succinate, an amphiphilic carbohydrate nanoparticle, and epsilon-polylysine to improve lipid oxidative stability of emulsions. J Agric Food Chem. 2010 Jan. 13; 58(1):660-7; Scheffler S L, et al. In vitro digestibility and emulsification properties of phytoglycogen octenyl succinate. J Agric Food Chem. 2010 58(8):5140-6; and Huang, L., & Yao, Y. Particulate structure of phytoglycogen nanoparticles probed using amyloglucosidase. Carbohydrate Polymers, 2011, 83:1165-1171; which describe processes of isolating phytoglycogen from sweet corn; the disclosures of all of which are incorporated by reference in their entirety.
Glycogen can also be obtained from yeasts according to various methods as described, for example, in international patent application WO/1997/021828; U.S. Pat. No. 6,146,857; and Northcote D. The molecular structure and shape of yeast glycogen. Biochem J. 1953, 53(3): 348-352; the disclosures of which are incorporated by reference in their entirety.
Glycogen can also be obtained from bacteria according to various methods, as described, for example, in Levine S, et al. Glycogen of enteric bacteria. J Bacteriol. 1953, 66(6): 664-670; Sigal N, et al. Glycogen accumulation by wild-type and uridine diphosphate glucose pyrophosphorylase-negative strains of escherichia coli. Arch Biochem Biophys. 1964, 108:440-451; Chargaff E. & H. Moore. On bacterial glycogen: the isolation from avian tubercle bacilli of a polyglucosan of very high particle weight. J. Biol. Chem. 1944, 155: 493-501; Yoo S H, et al. Characterization of cyanobacterial glycogen isolated from the wild type and from a mutant lacking of branching enzyme. Carbohydr Res. 2002, 337(21-23):2195-203; Schneegurt M A, et al. Composition of the carbohydrate granules of the cyanobacterium, Cyanothece sp. strain ATCC 51142. Arch Microbiol. 1997, 167(2-3):89-98; and Schneegurt M A, et al. Oscillating behavior of carbohydrate granule formation and dinitrogen fixation in the cyanobacterium Cyanothece sp. strain ATCC 51142. Bacteriol. 1994, 176(6): 1586-1597; the contents of which are incorporated herein by reference in their entirety.
Glycogen and phytoglycogen may also be prepared using biosynthetic methods. U.S. Pat. No. 7,670,812 describes a process for the biosynthetic production of glycogen-like polysaccharides by exposing a mixture of enzymes to low molecular weight dextrins.
Glycogen and phytoglycogen may also be obtained from commercial sources. E.g. phytoglycogen derived from corn is sold commercially by IKEDA CORPORATION, Japan and KEWPIE CORPORATION, Japan; enzymatically synthesized glycogen is sold commercially under the name of BIOGLYCOGEN by Ezaki Glico Co.; LABORATOIRES SÉROBIOLOGIQUES S.A. (FRANCE) sells a glycogen derived from marine sources under the name DERMOSACCHARIDES® GY. Glycogen is also sold as a co-precipitant for the precipitation of nucleic acids and is offered commercially by many companies, such as Roche, Sigma-Aldrich, SERVA Electrophoresis GmbH, and Life Technologies.
Applications of glycogen, phytoglycogen and related glycogen-like material have been suggested.
U.S. Pat. No. 6,451,362 describes the use of phytoglycogen derived from sweet corn as a coating layer for ready-to-eat cereals, which slows down wetting of the cereal flakes and prolongs crunchiness. International patent application WO/2011/062999A2 describes the use of chemically modified phytoglycogen as an emulsification aid for food applications. United States patent application publication no. 201110269849A1 describes the use of chemically modified phytoglycogen to improve oxidative stability of lipids in food applications.
Japanese patent application JP1999000044901 proposes the use of phytoglycogen as an additive for hair formulations that imparts improved combing properties and shiny appearance to hair. U.S. Pat. No. 6,224,889 provides a skincare cosmetic composition that includes glycogen as one of several components suitable for protecting human skin from the effects of cold. United States patent application publication no. 2010/0273736 provides cosmetic formulations containing glycogen as the active ingredient for a skin softening/smoothing effect and U.S. Pat. No. 5,093,109 describes glycogen as an anti-aging agent that can be used for those purposes in cosmetic formulations. Japanese patent application JP-A-62-178 505 describes the use of glycogen as an emollient and hydrating agent in cosmetic formulations. United States patent application publication no. 2004-0052749 describes an aqueous gel for the skin comprising creatinine or a creatinine derivative, glycogen and phopholipid, which is claimed to have a revitalizing effect and to provide UV protection.
U.S. Pat. No. 4,803,075 discloses glycogen (along with maltose) as a biocompatible fluid lubricant that improves the intrudability of injectable implant biomaterials.
There is a growing need for incorporation of natural, non-toxic and biodegradable materials in food, personal care, paints, coating and other industrial products to replace petroleum-based chemicals. Polyfunctional additives in particular are in high demand since reducing the number of ingredients makes the formulation process easier and lowers the formulation cost. Further, in the personal care industry, ingredients that can be provided in concentrated liquid form are highly desirable since it simplifies the formulation process and enables easy handling by automatic dispensers and metering pumps.